AskAI History in MyFam360 — Pin, Re-Run, and Why the Cap Doesn't Reset

The hardest part of using a financial assistant isn’t getting an answer once. It’s getting the same useful answer reliably, every month, with low effort. Most chatbot interfaces lose this completely — every session starts blank, and remembering what to ask is more work than asking it.

MyFam360’s AskAI was originally built that way too — fire a question, get an answer, lose both. The recent updates fixed that. AskAI now has durable server-side history, pinning, search, and one-click Run Again — designed around the assumption that you’ll ask the same set of questions repeatedly and want to compare answers across months.

This post explains how the history flow works, what the daily cap actually counts, and why pinning is the most underrated feature in the app.

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What Got Built

A new ask_ai_history table persists every AskAI interaction:

Field	Purpose
question	The user’s prompt
answer	The LLM’s response
is_pinned	Boolean — pinned questions sort to top and survive Clear
asked_by_user_id	Which family member asked
family_group_id	Family scope
created_at	Timestamp
aggregate_summary_used	The minimised payload sent to the LLM (audit trail)

Two new endpoints back it: GET /families/{id}/ask-ai/history and DELETE /families/{id}/ask-ai/history. Every AskAI request automatically inserts a row.

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The History UI

Open Insights → AskAI. The page is split into two zones:

Left: Composer

A text field where you type a question, plus a list of suggested questions for inspiration. The submit button is disabled when you’re at the daily cap (more below).

Right: History

A grouped list of past questions and answers, organised into:

• Pinned — at the top, with a yellow star icon
• Today — questions asked since midnight UTC
• Yesterday — questions asked the previous UTC day
• Older — everything else, sorted newest first

A search box filters by question text (substring, case-insensitive). Clear History wipes everything except pinned questions — pinned items are the exception by design.

Each row has three actions:

• Run Again — re-issues the same question against current data, appends a new history row
• Pin / Unpin — toggle the is_pinned flag
• Delete — soft-delete the single row

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The Three-Per-Day Cap

The cap is enforced against a durable audit_logs count, not against the visible history list. Specifically:

SELECT COUNT(*) FROM audit_logs
WHERE family_group_id = ?
  AND entity_type = 'ask_ai_request'
  AND created_at >= today_utc_midnight

If the count is ≥ Settings.ASK_AI_DAILY_GROUP_CAP (default 3), the next request returns 429.

The decoupling matters for two reasons:

1. Clearing history doesn’t reset the cap. A user who hits the cap can’t just clear history and resume — the audit count is independent.
2. The audit trail is permanent. Even after history is cleared, you (or admin support) can see how AskAI was used.

The cap is admin-configurable via the App Settings page (Admin → Project Features → App Settings → ask_ai_daily_group_cap). The default of 3 is conservative for the rollout; expect this to evolve.

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Why Pinning Is the Most Important Feature

The default AskAI workflow without pinning:

1. Day 1: ask “What was my biggest spend?” — get answer
2. Day 30: try to remember what you asked — re-type it slightly differently — get a slightly different answer
3. Day 60: drift

The default AskAI workflow with pinning:

1. Day 1: ask the question, pin it, get answer
2. Day 30: open AskAI, tap Run Again on the pinned question, get this month’s answer
3. Day 60: same, same, same — you have a 3-month trend

The cost is one tap (Pin) on the day you first ask. The benefit accrues for the entire lifetime of your usage of MyFam360.

The four questions I’d recommend pinning, in order of usefulness:

1. “What were my top 5 spending categories last month?” — the canonical monthly review opener.
2. “How did my savings rate compare to the last three months?” — surfaces drift early.
3. “Which budgets did I exceed last month, and by how much?” — turns budget adherence into a checklist.
4. “What recurring expenses have I logged in the last 60 days I might have forgotten about?” — the subscription audit prompt.

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The Duplicate-Question Guard

If you type a question that exactly matches a recent history entry (within the same UTC day), MyFam360 surfaces the existing entry without consuming a daily quota slot. The guard is exact-match — typo-tolerant deduplication would risk surfacing the wrong entry.

The guard does not apply to Run Again. Run Again is the explicit “re-run against current data” action — it always issues a fresh request (and counts against the daily cap).

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What AskAI Doesn’t See

The minimisation gateway (llm_minimization_service.py) is the architectural firewall between your data and the external LLM. It only constructs aggregate payloads:

• Category totals for the requested time window
• Monthly summaries (income, expense, net)
• Budget adherence percentages
• Recurring expense list with frequencies (no amounts beyond totals)
• Savings goal progress

It does not send:

• Individual transaction descriptions
• Merchant names
• Account identifiers
• Transaction IDs
• Member names tied to specific transactions

This is hard-coded in the service — there’s no path in the codebase for AskAI to receive transaction-level fields. The full architecture is documented in the AI privacy post.

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Cost and Quota Trade-Offs

AskAI is expensive to serve. Each request hits an external LLM (OpenAI or Gemini, configurable via LLM_PROVIDER), and the cost is roughly proportional to the input + output token count. The minimisation gateway helps by keeping inputs small, but each request still costs real money.

The 3-per-day cap maps directly to a budget the team can sustain across the user base. If usage trends down (people pin and re-run more, asking fewer net-new questions), the cap may rise. If costs come down (model prices fall), the cap may rise.

The right mental model: AskAI is a finite, replenishing resource — not an unlimited chatbot.

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What This Means For You

Spend 10 minutes today setting up your monthly review:

1. Ask 3–4 of the questions you’d want answered every month.
2. Pin each one.
3. Set a recurring calendar reminder on the 1st of each month: “Open AskAI → Run Again on pinned”.

After two months you’ll have a trend dataset. After six months you’ll have a rolling financial dashboard you didn’t have to design.

The hardest version of personal finance management is staying consistent. Pinning is how AskAI helps you do that.

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See Also

• How AI Features Work Without Seeing Your Personal Data — the full LLM minimisation architecture
• How to Read Your Spending Reports in MyFam360 — pairs well with AskAI for monthly review
• What’s New in MyFam360 — the Roundup